1-(Bromomethyl)-2-(trifluoromethyl)benzene → Ethyl 2,2-difluoro-3-(2-(trifluoromethyl)phenyl)propanoate

HRID 1050180Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[F:13][C:14]([F:21])(I)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CS(C)=O.[Cu]>[F:13][C:14]([F:21])([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of 1-(bromomethyl)-2-(trifluoromethyl)benzene (0.5 g, 2.092 mmol) in DMSO (10 mL) was added ethyl 2,2-difluoro-2-iodoacetate (0.410 mL, 2.000 mmol) and copper (0.439 g, 6.90 mmol) at rt. The mixture was stirred at 20° C. for 10 h. The mixture was extracted with EA, washed with brine, and the organic layer was concentrated to give ethyl 2,2-difluoro-3-(2-(trifluoromethyl)phenyl)propanoate (320 mg, 0.981 mmol, 46.9% yield): 1H NMR (400 MHz, CD3OD-d4) δ 7.72 (d, J=7.8 Hz, 1H), 7.60-7.45 (m, 3H), 4.26 (d, J=7.1 Hz, 2H), 3.63 (t, J=16.9 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H).

Workup

extractionThe mixture was extracted with EA
washwashed with brine
concentrationthe organic layer was concentrated

Sources & evidence

ORD record: ord-6048f5cc09ba4517b0faa2ef72f235c4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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